davidtsai

Day 13 of 3031 August 2026

The person across from you

A while back I met with a life coach who will bring in a little over a million this year. He told me that’s his average — and a bit on the lower end, but still good.

Naturally, I asked what scaling looks like for him. How he was thinking about a wider reach, a bigger audience, digital products or courses. More clients.

He said none of it.

Instead, he wants to go deeper with the people he already works with. The ones whose history and stories he knows. The people he already cares deeply about and is already invested in.

Which made me pause.

Because everything right now is pulling the other direction. More output, more reach, more leverage, more speed. Our entire economy is being rebuilt to autonomously serve the anonymous at scale.

But the people who got there tend to regret what it cost them.

Brian Chesky, worth over ten billion, said on The Diary Of A CEO that one of the great regrets of his life was losing touch with the people who knew him before any of the success. The sister he went weeks without calling. Childhood friends he didn’t speak to for nearly twenty years. He said life is more than climbing a ladder and getting to the top and realizing you aren’t much higher than you were before.

The rich regrets all sound like a version of that.

None of them regret the scale or the success.

They regret the people they left behind.

The coach I spoke with isn’t wiser than the rest of us. He just saw it earlier. He figured out that the people already in his life are the point, not the stepping stone before something bigger.

The person across from you is not a smaller opportunity than the thousands of anonymous strangers who don’t know your name.

Deeper relationships > more connections > success.